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  1. $3,035 to $11,599/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $2,958 to $11,468/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $2,532 to $10,440/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $1,846 to $6,200/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  9. $1,779 to $4,754/night

    Gorgeous Renovated 1937 Plantation Style Beach House 50 ...

    5 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  12. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  13. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  15. $1,443 to $5,169/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $1,349 to $1,609/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $1,220 to $4,156/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $1,202 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $1,202 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $1,154 to $5,720/night

    Wailea Beach Villa M312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $1,126 to $4,236/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $1,096 to $5,113/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $1,074 to $2,182/night

    Spindrift Kauai

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
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  35. $1,068 to $2,913/night

    King Hale

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $1,038 to $4,344/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,038 to $5,013/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $1,038 to $3,879/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $1,017 to $3,146/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $989 to $2,906/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $987 to $4,528/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $981 to $4,337/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $961 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $935 to $1,767/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $923 to $4,451/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $923 to $3,670/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $923 to $2,740/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  65. $923 to $2,546/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $922 to $3,198/night

    Maui Dolphin House

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  69. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $918 to $2,312/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $898 to $2,525/night

    Niulani Lanikai- Kauai Beach House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $866 to $3,860/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $865 to $3,810/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $848 to $1,916/night

    Hale Ohana Nui

    5 Bedrooms6.5 BathroomsSleeps 12
    3 nights minstay
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $837 to $1,583/night

    Kapalua Ridge Villas-#323

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $825 to $1,320/night

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $824 to $1,045/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $808 to $2,974/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $802 to $3,792/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $767 to $2,974/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $763 to $1,556/night

    Kamapua'a Hale

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $751 to $808/night

    Molokama Vacation Home in Hanalei Bay Near Beach

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $750 to $3,970/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $735 to $1,575/night

    Holua House#28

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $725 to $1,260/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $721 to $2,362/night

    Noelani 306

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $719 to $1,865/night

    Nakoa Kai

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $716 to $2,130/night

    Wailea Elua 2109

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $701 to $3,465/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $695 to $1,243/night

    Puu Poa 303

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $687 to $1,176/night

    Mana Kai #412

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $668 to $2,676/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $659 to $879/night

    Kona Bay Hale

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $659 to $2,025/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $656 to $2,986/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $606 to $2,300/night

    Makena Surf A204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $605 to $1,243/night

    Cliffs 8301

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $604 to $2,924/night

    Makena Surf F201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $603 to $2,216/night

    Kauai Poipu Kapili 51

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $577 to $1,644/night

    Mana Kai #403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $577 to $1,626/night

    Big Island Holua Kai 111

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $577 to $2,098/night

    Wailea Ekahi 48A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $576 to $1,374/night

    Mana Kai #203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $572 to $2,139/night

    Maui Hill 66

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $569 to $2,093/night

    Big Island Waiulaula at Mauna Kea J201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $554 to $1,824/night

    Mana Kai #705

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $549 to $1,381/night

    Big Island Holua Kai 7066

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $547 to $1,687/night

    Kauai Villas at Poipu Kai E211

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $545 to $1,833/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $536 to $1,499/night

    Mana Kai #307

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $528 to $1,513/night

    Royal Mauian 206

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $520 to $625/night

    Kauai Tree House

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $520 to $1,689/night

    Honua Kai Hokulani 310

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $520 to $2,059/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $499 to $735/night

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $485 to $1,700/night

    Mana Kai #805

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $477 to $2,169/night

    Wailea Ekahi 26A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $474 to $1,306/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $469 to $1,791/night

    Big Island Kolea 11C

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $469 to $1,789/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $467 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $467 to $1,464/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $467 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $467 to $1,449/night

    Mana Kai #815

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $466 to $1,650/night

    Kauai Kiahuna Plantation #64

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $461 to $1,510/night

    Kapalua Ridge Villas-#2212

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $458 to $1,608/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $441 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations